Tech-savvy ops help needed with QuickBooks + things

Hi there.

I run a small but growing short-term rental business in Chicago. Over the last two years, I’ve been in nonstop build mode: setting up units, designing spaces, solving problems, and keeping things moving forward.

The good news: the business is finally starting to work. Operations are tight, and I am in the top 1% of Airbnb hosts in the city.
The less glamorous news: a lot of the systems underneath it are very close to being good… but not quite tidy yet. And a few are still abstract 'oh, that might work' thoughts written in pencil on post it notes.

That’s where you come in.

I’m a highly creative, curious, and generally pleasant 45-year-old gay guy who is very good at vision, design, and momentum but noticeably less good at sustained technical cleanup, bookkeeping mechanics, and digital systems. I honestly miss the days of fax machines and miss my beige rolodex.

My brain absolutely thrives when things are organized and logical. I just need help getting them there and keeping them that way.

The immediate need (Phase 1)

This role starts with a serious QuickBooks Online cleanup for a multi-property Airbnb business.

Specifically:

Cleaning up roughly three years of QuickBooks data

Reconciling accounts with shared Airbnb payouts

Understanding the difference between Airbnb gross income reporting and actual cash received

Helping evaluate and implement TallyBreeze, which aligns Airbnb data with IRS reporting logic

Rolling back and re-classifying transactions if needed so everything is clean and consistent

Making thoughtful adjustments to the chart of accounts when it improves accuracy

Accuracy matters more to me than speed. I intentionally did not file taxes last year because the business will show a loss, and I want this done correctly and defensibly rather than rushed or papered over.

This is real cleanup work, not a tune-up.

I’m collaborative, engaged, and I ask questions because I want to understand the “why.” I’m not looking to micromanage, but I will want visibility and clarity.

I’ll be honest: my natural reaction to complexity is a calm, polite paranoia. I don’t panic or spiral, but I do want things to make sense, be explainable, and be solid.

If you’re someone who:

likes making systems tidy

isn’t rattled by a bit of mess at the start

can explain what you’re doing and why

enjoys turning “almost there” into “done”

we will likely work very well together.

Phase 2 (after cleanup)

Once the foundation is solid, this role can expand into broader operational support, including:

Ongoing bookkeeping maintenance

Helping integrate tools like TallyBreeze and Lettuce

List and project follow-through

Light website or tech support (oh, god, my email inbox is terrifying)

Walking properties, helping with setup, inventory, and organization

Think of this as a tech-savvy, detail-oriented operations manager, not a task rabbit.

Location: In person, Ravenswood (North Side Chicago)

Schedule: Flexible (very), part-time

Timing: Conversations now; role begins early March when I have cash flow again.

We will have a 10 minute zoom chat, then if it seems like a possible good fit I’m happy to pay for an hour upfront to walk through the situation and talk approach before committing to next steps.

If this sounds like work you’d enjoy, send a short note about your experience with:

QuickBooks

tech tools or integrations

working with creative but slightly distracted people

Thanks.